JP2007506734A - 新規な化合物 - Google Patents

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Publication number

JP2007506734A

JP2007506734A JP2006527944A JP2006527944A JP2007506734A JP 2007506734 A JP2007506734 A JP 2007506734A JP 2006527944 A JP2006527944 A JP 2006527944A JP 2006527944 A JP2006527944 A JP 2006527944A JP 2007506734 A JP2007506734 A JP 2007506734A

Authority

JP

Japan

Prior art keywords

hydroxy

pyridin

indole

alkyl

sulfonyl

Prior art date

2003-09-24

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Pending

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 287
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 127
• 150000003839 salts Chemical class 0.000 claims abstract description 41
• 239000001257 hydrogen Substances 0.000 claims abstract description 33
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
• 238000000034 method Methods 0.000 claims abstract description 31
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 29
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 24
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 20
• 150000002367 halogens Chemical class 0.000 claims abstract description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
• 238000002360 preparation method Methods 0.000 claims abstract description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
• 230000008569 process Effects 0.000 claims abstract description 9
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 4
• 239000002585 base Substances 0.000 claims description 117
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 103
• 238000006243 chemical reaction Methods 0.000 claims description 103
• 239000002904 solvent Substances 0.000 claims description 97
• -1 6-Cyano-2-hydroxy-1H-indol-3-yl Chemical group 0.000 claims description 81
• 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims description 37
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 33
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
• 238000011282 treatment Methods 0.000 claims description 29
• 239000003153 chemical reaction reagent Substances 0.000 claims description 28
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 27
• 201000010099 disease Diseases 0.000 claims description 27
• 125000000623 heterocyclic group Chemical group 0.000 claims description 27
• 230000002265 prevention Effects 0.000 claims description 27
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 24
• 206010012289 Dementia Diseases 0.000 claims description 22
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
• 150000001412 amines Chemical class 0.000 claims description 20
• 125000005843 halogen group Chemical group 0.000 claims description 20
• 239000002253 acid Substances 0.000 claims description 18
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 17
• 208000024827 Alzheimer disease Diseases 0.000 claims description 17
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 17
• 239000012458 free base Substances 0.000 claims description 17
• 208000010877 cognitive disease Diseases 0.000 claims description 16
• 150000002431 hydrogen Chemical class 0.000 claims description 15
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 14
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 13
• 238000004519 manufacturing process Methods 0.000 claims description 12
• 238000010992 reflux Methods 0.000 claims description 12
• 150000003457 sulfones Chemical class 0.000 claims description 12
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 11
• 230000007850 degeneration Effects 0.000 claims description 11
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
• 150000003973 alkyl amines Chemical class 0.000 claims description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
• JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims description 10
• 201000011240 Frontotemporal dementia Diseases 0.000 claims description 9
• 241000124008 Mammalia Species 0.000 claims description 9
• 230000004913 activation Effects 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 9
• 201000004384 Alopecia Diseases 0.000 claims description 8
• 208000018737 Parkinson disease Diseases 0.000 claims description 8
• QAVVLZHCFJNBLR-UHFFFAOYSA-N 2-hydroxy-3-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-1H-indole-5-carboxylic acid Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C(O)=O)N=C1 QAVVLZHCFJNBLR-UHFFFAOYSA-N 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 230000006870 function Effects 0.000 claims description 7
• 201000000980 schizophrenia Diseases 0.000 claims description 7
• 208000020925 Bipolar disease Diseases 0.000 claims description 6
• 208000028698 Cognitive impairment Diseases 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 230000009435 amidation Effects 0.000 claims description 6
• 238000007112 amidation reaction Methods 0.000 claims description 6
• 208000028683 bipolar I disease Diseases 0.000 claims description 6
• 206010012601 diabetes mellitus Diseases 0.000 claims description 6
• 230000002140 halogenating effect Effects 0.000 claims description 6
• 206010027175 memory impairment Diseases 0.000 claims description 6
• AJFUNKWEQCVOKI-UHFFFAOYSA-N n-(2-methoxyethyl)-2-oxo-1,3-dihydroindole-5-carboxamide Chemical compound COCCNC(=O)C1=CC=C2NC(=O)CC2=C1 AJFUNKWEQCVOKI-UHFFFAOYSA-N 0.000 claims description 6
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
• JJAHGJDXTZIKLJ-UHFFFAOYSA-N 2-hydroxy-3-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-1H-indole-5-carbonitrile Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C#N)N=C1 JJAHGJDXTZIKLJ-UHFFFAOYSA-N 0.000 claims description 5
• 206010019196 Head injury Diseases 0.000 claims description 5
• 241000282412 Homo Species 0.000 claims description 5
• 231100000360 alopecia Toxicity 0.000 claims description 5
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 5
• 230000001684 chronic effect Effects 0.000 claims description 5
• 230000008878 coupling Effects 0.000 claims description 5
• 238000010168 coupling process Methods 0.000 claims description 5
• 238000005859 coupling reaction Methods 0.000 claims description 5
• JGHOWLLTSGGZJT-UHFFFAOYSA-N methyl 2-hydroxy-3-[5-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]-1H-indole-5-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2NC(O)=C1C(N=C1)=CC=C1CN1CCN(C)CC1 JGHOWLLTSGGZJT-UHFFFAOYSA-N 0.000 claims description 5
• MIFWNNROFUVTRK-UHFFFAOYSA-N 1-(6-chloropyridin-3-yl)sulfonyl-4-(2-pyrrolidin-1-ylethyl)piperazine Chemical compound C1=NC(Cl)=CC=C1S(=O)(=O)N1CCN(CCN2CCCC2)CC1 MIFWNNROFUVTRK-UHFFFAOYSA-N 0.000 claims description 4
• ODWXXJVCDVLFHO-UHFFFAOYSA-N 2-[4-(6-chloropyridin-3-yl)sulfonylpiperazin-1-yl]-n,n-dimethylethanamine Chemical compound C1CN(CCN(C)C)CCN1S(=O)(=O)C1=CC=C(Cl)N=C1 ODWXXJVCDVLFHO-UHFFFAOYSA-N 0.000 claims description 4
• PDWUYBUKLNGRBU-UHFFFAOYSA-N 2-oxo-n-(pyridin-2-ylmethyl)-1,3-dihydroindole-5-carboxamide Chemical compound C=1C=C2NC(=O)CC2=CC=1C(=O)NCC1=CC=CC=N1 PDWUYBUKLNGRBU-UHFFFAOYSA-N 0.000 claims description 4
• RTYCNXDZALHJGQ-UHFFFAOYSA-N 2-oxo-n-propyl-1,3-dihydroindole-5-carboxamide Chemical compound CCCNC(=O)C1=CC=C2NC(=O)CC2=C1 RTYCNXDZALHJGQ-UHFFFAOYSA-N 0.000 claims description 4
• BHGFDIYEFUUCNM-UHFFFAOYSA-N 4-(6-chloropyridin-3-yl)sulfonylmorpholine Chemical compound C1=NC(Cl)=CC=C1S(=O)(=O)N1CCOCC1 BHGFDIYEFUUCNM-UHFFFAOYSA-N 0.000 claims description 4
• MPMJQNJEXNCCTR-UHFFFAOYSA-N 4-[2-[4-(6-chloropyridin-3-yl)sulfonylpiperazin-1-yl]ethyl]morpholine Chemical compound C1=NC(Cl)=CC=C1S(=O)(=O)N1CCN(CCN2CCOCC2)CC1 MPMJQNJEXNCCTR-UHFFFAOYSA-N 0.000 claims description 4
• FKJJOWPHIXDNDD-UHFFFAOYSA-N 6-bromo-2-oxo-n-propan-2-yl-1,3-dihydroindole-5-carboxamide Chemical compound C1=C(Br)C(C(=O)NC(C)C)=CC2=C1NC(=O)C2 FKJJOWPHIXDNDD-UHFFFAOYSA-N 0.000 claims description 4
• ADHVDPXBWORXMJ-UHFFFAOYSA-N 6-bromo-n-(2-methoxyethyl)-2-oxo-1,3-dihydroindole-5-carboxamide Chemical compound C1=C(Br)C(C(=O)NCCOC)=CC2=C1NC(=O)C2 ADHVDPXBWORXMJ-UHFFFAOYSA-N 0.000 claims description 4
• IOBHGRBPVCQMNI-UHFFFAOYSA-N 6-chloro-1-oxidopyridin-1-ium-3-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)[N+]([O-])=C1 IOBHGRBPVCQMNI-UHFFFAOYSA-N 0.000 claims description 4
• KTSVLYHMXKUEFX-UHFFFAOYSA-N 6-chloro-n-(2-pyrrolidin-1-ylethyl)pyridine-3-sulfonamide Chemical compound C1=NC(Cl)=CC=C1S(=O)(=O)NCCN1CCCC1 KTSVLYHMXKUEFX-UHFFFAOYSA-N 0.000 claims description 4
• 201000010374 Down Syndrome Diseases 0.000 claims description 4
• 208000027534 Emotional disease Diseases 0.000 claims description 4
• 208000023105 Huntington disease Diseases 0.000 claims description 4
• 208000014060 Niemann-Pick disease Diseases 0.000 claims description 4
• 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 4
• 239000004480 active ingredient Substances 0.000 claims description 4
• 210000000988 bone and bone Anatomy 0.000 claims description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
• 230000006999 cognitive decline Effects 0.000 claims description 4
• 230000001054 cortical effect Effects 0.000 claims description 4
• 230000007423 decrease Effects 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• HWYXWVWNJLATGW-UHFFFAOYSA-N methyl 2-hydroxy-3-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-1H-indole-5-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2NC(O)=C1C(N=C1)=CC=C1S(=O)(=O)N1CCN(C)CC1 HWYXWVWNJLATGW-UHFFFAOYSA-N 0.000 claims description 4
• NKWOVQJVMASPAS-UHFFFAOYSA-N n-(2-acetamidoethyl)-2-oxo-1,3-dihydroindole-5-carboxamide Chemical compound CC(=O)NCCNC(=O)C1=CC=C2NC(=O)CC2=C1 NKWOVQJVMASPAS-UHFFFAOYSA-N 0.000 claims description 4
• SLGCBXXXLUKEKX-UHFFFAOYSA-N n-(2-cyanoethyl)-2-oxo-1,3-dihydroindole-5-carboxamide Chemical compound N#CCCNC(=O)C1=CC=C2NC(=O)CC2=C1 SLGCBXXXLUKEKX-UHFFFAOYSA-N 0.000 claims description 4
• KBROTFGEOBLMGP-UHFFFAOYSA-N n-(3-methoxypropyl)-2-oxo-1,3-dihydroindole-5-carboxamide Chemical compound COCCCNC(=O)C1=CC=C2NC(=O)CC2=C1 KBROTFGEOBLMGP-UHFFFAOYSA-N 0.000 claims description 4
• PGKRDJHKIISUEY-UHFFFAOYSA-N n-[(3-methoxyphenyl)methyl]-2-oxo-1,3-dihydroindole-5-carboxamide Chemical compound COC1=CC=CC(CNC(=O)C=2C=C3CC(=O)NC3=CC=2)=C1 PGKRDJHKIISUEY-UHFFFAOYSA-N 0.000 claims description 4
• VQHUCMCIWMZMDP-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-2-oxo-1,3-dihydroindole-5-carboxamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)C1=CC=C(NC(=O)C2)C2=C1 VQHUCMCIWMZMDP-UHFFFAOYSA-N 0.000 claims description 4
• IHOSFZHEASIKRF-UHFFFAOYSA-N n-[2-(6-chloropyrimidin-4-yl)oxyethyl]-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C(C)C)CCOC1=CC(Cl)=NC=N1 IHOSFZHEASIKRF-UHFFFAOYSA-N 0.000 claims description 4
• XHQSKBZJTKNTAV-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-oxo-1,3-dihydroindole-5-carboxamide Chemical compound CN(C)CCNC(=O)C1=CC=C2NC(=O)CC2=C1 XHQSKBZJTKNTAV-UHFFFAOYSA-N 0.000 claims description 4
• AQIXDVXRDYWZHY-UHFFFAOYSA-N n-[2-[4-(6-chloropyridin-3-yl)sulfonylpiperazin-1-yl]ethyl]-n-propylpropan-1-amine Chemical compound C1CN(CCN(CCC)CCC)CCN1S(=O)(=O)C1=CC=C(Cl)N=C1 AQIXDVXRDYWZHY-UHFFFAOYSA-N 0.000 claims description 4
• QPUWDWDRMYYLKC-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-2-oxo-1,3-dihydroindole-5-carboxamide Chemical compound CN(C)CCCNC(=O)C1=CC=C2NC(=O)CC2=C1 QPUWDWDRMYYLKC-UHFFFAOYSA-N 0.000 claims description 4
• 210000005036 nerve Anatomy 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 4
• 208000000170 postencephalitic Parkinson disease Diseases 0.000 claims description 4
• 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 4
• DZDKVQGQVYLFNO-UHFFFAOYSA-N tert-butyl 4-(6-chloropyridin-3-yl)sulfonylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1S(=O)(=O)C1=CC=C(Cl)N=C1 DZDKVQGQVYLFNO-UHFFFAOYSA-N 0.000 claims description 4
• DYRLZFVNXVAEDL-UHFFFAOYSA-N 1-(6-chloropyridin-3-yl)sulfonyl-4-(2-methoxyethyl)piperazine Chemical compound C1CN(CCOC)CCN1S(=O)(=O)C1=CC=C(Cl)N=C1 DYRLZFVNXVAEDL-UHFFFAOYSA-N 0.000 claims description 3
• IJVVJCPEIIGOMP-UHFFFAOYSA-N 2-hydroxy-3-(5-piperazin-1-ylsulfonylpyridin-2-yl)-1H-indole-6-carbonitrile hydrochloride Chemical compound Cl.OC=1NC2=CC(C#N)=CC=C2C=1C(N=C1)=CC=C1S(=O)(=O)N1CCNCC1 IJVVJCPEIIGOMP-UHFFFAOYSA-N 0.000 claims description 3
• VVGAYLKTCQGMFS-UHFFFAOYSA-N 2-hydroxy-3-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-1H-indole-5-carboxamide hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C(N)=O)N=C1 VVGAYLKTCQGMFS-UHFFFAOYSA-N 0.000 claims description 3
• HFLLBRVZKPPKCH-UHFFFAOYSA-N 2-hydroxy-3-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-1H-indole-5-carboxylic acid hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C(O)=O)N=C1 HFLLBRVZKPPKCH-UHFFFAOYSA-N 0.000 claims description 3
• UKTGVBALDDUERE-UHFFFAOYSA-N 2-hydroxy-3-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-1H-indole-5-sulfonamide hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)S(N)(=O)=O)N=C1 UKTGVBALDDUERE-UHFFFAOYSA-N 0.000 claims description 3
• BLCRGIDHHLALSS-UHFFFAOYSA-N 2-hydroxy-3-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-1H-indole-6-carboxamide hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC=C(C=C3NC=2O)C(N)=O)N=C1 BLCRGIDHHLALSS-UHFFFAOYSA-N 0.000 claims description 3
• RSYANYRACLBNQK-UHFFFAOYSA-N 2-hydroxy-3-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-N-(2-methylsulfonylethyl)-1H-indole-5-carboxamide hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C(=O)NCCS(C)(=O)=O)N=C1 RSYANYRACLBNQK-UHFFFAOYSA-N 0.000 claims description 3
• ANSNQPHCYVTRCH-UHFFFAOYSA-N 2-hydroxy-3-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-N-(2-sulfamoylethyl)-1H-indole-5-carboxamide hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C(=O)NCCS(N)(=O)=O)N=C1 ANSNQPHCYVTRCH-UHFFFAOYSA-N 0.000 claims description 3
• CELCSPNSMRHPFE-UHFFFAOYSA-N 2-hydroxy-3-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-N-(2-thiophen-2-ylethyl)-1H-indole-5-carboxamide hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C(=O)NCCC=2SC=CC=2)N=C1 CELCSPNSMRHPFE-UHFFFAOYSA-N 0.000 claims description 3
• LJXILSGLQWSDEO-UHFFFAOYSA-N 2-hydroxy-3-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-N-(thiophen-2-ylmethyl)-1H-indole-5-carboxamide hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C(=O)NCC=2SC=CC=2)N=C1 LJXILSGLQWSDEO-UHFFFAOYSA-N 0.000 claims description 3
• OOGFVNLNSHPJFJ-UHFFFAOYSA-N 2-hydroxy-3-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-N-[2-(2-oxoimidazolidin-1-yl)ethyl]-1H-indole-5-carboxamide hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C(=O)NCCN2C(NCC2)=O)N=C1 OOGFVNLNSHPJFJ-UHFFFAOYSA-N 0.000 claims description 3
• LTGBJZKVNZDLMP-UHFFFAOYSA-N 2-hydroxy-3-[5-(4-methylpiperazin-1-yl)sulfonylpyridin-2-yl]-N-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-indole-5-carboxamide hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C1=CC=C(C=2C3=CC(=CC=C3NC=2O)C(=O)NCCCN2C(CCC2)=O)N=C1 LTGBJZKVNZDLMP-UHFFFAOYSA-N 0.000 claims description 3
• UZWYFTWHMGPOHV-UHFFFAOYSA-N 2-hydroxy-3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-N-(2-sulfamoylethyl)-1H-indole-5-carboxamide hydrochloride Chemical compound Cl.C12=CC(C(=O)NCCS(=O)(=O)N)=CC=C2NC(O)=C1C(N=C1)=CC=C1CN1CCOCC1 UZWYFTWHMGPOHV-UHFFFAOYSA-N 0.000 claims description 3
• QTCXKQVDWNKNMJ-UHFFFAOYSA-N 2-hydroxy-3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-N-(oxolan-2-ylmethyl)-1H-indole-5-carboxamide hydrochloride Chemical compound Cl.OC=1NC2=CC=C(C(=O)NCC3OCCC3)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 QTCXKQVDWNKNMJ-UHFFFAOYSA-N 0.000 claims description 3
• GFMUBUDSACTXNK-UHFFFAOYSA-N 2-hydroxy-3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-N-(pyridin-2-ylmethyl)-1H-indole-5-carboxamide hydrochloride Chemical compound Cl.OC=1NC2=CC=C(C(=O)NCC=3N=CC=CC=3)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 GFMUBUDSACTXNK-UHFFFAOYSA-N 0.000 claims description 3
• METBJTWBNFGAOU-UHFFFAOYSA-N 2-hydroxy-3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-N-(thiophen-2-ylmethyl)-1H-indole-5-carboxamide hydrochloride Chemical compound Cl.OC=1NC2=CC=C(C(=O)NCC=3SC=CC=3)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 METBJTWBNFGAOU-UHFFFAOYSA-N 0.000 claims description 3
• CGWKRTFHAJACSQ-UHFFFAOYSA-N 2-hydroxy-3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-N-[2-(2-oxoimidazolidin-1-yl)ethyl]-1H-indole-5-carboxamide hydrochloride Chemical compound Cl.OC=1NC2=CC=C(C(=O)NCCN3C(NCC3)=O)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 CGWKRTFHAJACSQ-UHFFFAOYSA-N 0.000 claims description 3
• KGVZUWKTNPMHRE-UHFFFAOYSA-N 2-hydroxy-3-[5-(morpholin-4-ylmethyl)pyridin-2-yl]-N-[[2-(trifluoromethoxy)phenyl]methyl]-1H-indole-5-carboxamide hydrochloride Chemical compound Cl.OC=1NC2=CC=C(C(=O)NCC=3C(=CC=CC=3)OC(F)(F)F)C=C2C=1C(N=C1)=CC=C1CN1CCOCC1 KGVZUWKTNPMHRE-UHFFFAOYSA-N 0.000 claims description 3
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